Timing, Options, & Opportunity Costs

(this should be a very short essay.)

Last night I had an hour-long phone chat with a very good friend of mine. The discussion centered around a big career move she was contemplating — something she had been planning on doing for a long time, with major positive implications for her well-being and life trajectory. The kind of adventure that reframes everything you do afterward; and the kind of opportunity that you kick yourself for not seizing while you’re young.

Yet, she was worried about the timing. Specifically:

• She’s doing great at her job, in a high-profile role that gives her access to notable professionals in her field.
• She stands to grow in influence & responsibility within her organization over the next 6–12 months.
• There are some vast (but uncertain and speculative) long-term rewards for performing well in her role over several years, provided that she stays in place and continues to do well.
• Meanwhile, several of her smartest friends have recently left their firms to start new, interesting ventures — and they’ve inquired about her availability for these projects. This is a different kind of work than both her current job and the big career jump she’s pondering, but it’s attractive and exciting nonetheless.
• No matter which direction she goes, leaving her current job means giving up financial security for at least a year and likely much longer.

I suspect where I’m going with this is rather transparent… There’s never a right time. Do it! Memento mori. Blah blah blah. Which is kind of my point, but not really.

Rather, my point is this: For talented people, the next career step is rarely ever clear and obvious. Great people are almost always faced with multiple compelling choices. For my friend, these risks; these anxieties; these switching penalties; these opportunity costs… she’s experiencing these strains precisely because she’s a talented person who other people want to work with. And since she’s always evaluating multiple intriguing career pathways, she is never free of the burden of comparing her current station to alternate paths.

(Quick pause… Yes, some people, e.g. PhD students intent on finishing their degrees, put themselves in situations where they’re impervious to alternatives. But it’s not as if those people don’t have other interesting opportunities they could pursue. They’ve just set up walls [attachment to sunk costs, self-identification with their field, social pressure, commitment to their word, etc.] that obscure and rebuff those opportunities.)

For instance, take someone like Sheryl Sandberg (certainly she has a high profile career). Let’s rewind to early 2008. Sheryl is running a large, important division within Google. She’s pals with Larry Summers. She hangs out at Davos. This is a person with lots of options.

Looking backwards from 2016, taking the COO job at Facebook seems obvious. But I sincerely doubt that it felt like a clear choice at the time. Joining a 4-year-old, cash burning, often controversial, nascent Internet business to work for a 24-year-old with (at the time) questionable leadership and communication skills… is… well, a risky career move. Not just in comparison to her contemporaneous gig at Google, but against all the other incredibly cool and lucrative things she could be doing instead. She made a great move, but I sincerely doubt it was an easy or obvious decision.

If Sheryl had been a crappy employee at Google, she would have been spared the discomfort of having to make these kinds of decisions: She wouldn’t have been having the conversation with Zuck in the first place.

To summarize…

… feeling conflicted about your next move isn’t a sign that something is wrong. It’s actually a sign that something is right. It means you’re doing well — that you’re the kind of person that other people want to invite into their grand plans. Or that you have the kind of skills that don’t require other people to permit or actualize. The better you are, and the better you do, the more you’ll feel this way.

Rather than delaying until the feeling passes — or until a more obvious path appears on the horizon, if ever — it may be a better strategy to gain comfort with this particular kind of stress. And perhaps even to seek it out, like a weightlifter who seeks the “burn”. It’s an uncomfortable feeling which indicates that growth and opportunity are ahead.

(Hit me up at pmmathieson if you want to discuss!)